The CRO Warning: He Was Winning Every Deal and About to Lose His Entire Team

What happens when you're winning every deal—but your team is quietly reaching its breaking point?

For Zach Sikora, CRO at Endor Labs, one of the biggest leadership lessons of his career came when he realized that driving results wasn't enough. His team was succeeding, but they were also fatigued and he risked creating a culture built around compliance rather than commitment. In this episode of Hunters and Unicorns, Simon Kouttis and Ollie Kuehne sit down with Zack to explore his journey from EMC and AppDynamics to People.ai and now Endor Labs, and the leadership lessons he learned along the way. Zack shares the moment his COO warned him that he might have a “mutiny” on his hands, why accountability has to come with empathy, and how explaining the “why,” using data, humanizing leadership, and giving people a voice transformed the way his team operated. The conversation also explores building a modern GTM organization, the role of RevOps and enablement, AI and application security, Endor Labs' growth journey, and why developing leaders is just as important as hiring more sales reps.

In this episode:

• The leadership mistake that nearly cost Zack his team's commitment

• Why winning doesn't mean your leadership approach is working

• The difference between compliance and commitment

• How to balance accountability with empathy

• Why leaders need to explain the “why” behind every decision

• How data can help bring sales teams along with the strategy

• Why RevOps and enablement should come before scaling headcount

• Building a culture focused on leadership development

• How AI is changing application security and software development

• Endor Labs' growth strategy and 100% channel approach

• What it really means to build a high-performing GTM organization

About Zack Sikora

Zack Sikora is Chief Revenue Officer at Endor Labs, with leadership experience at EMC, AppDynamics, People.ai, and Endor Labs. His experience spans high-growth technology, enterprise sales, go-to-market strategy, and revenue leadership, with a strong focus on building teams and developing leaders.

About Our Sponsor:

Big thanks to Aurasell for sponsoring this episode. Aurasell is an AI-native GTM platform designed to intelligently automate every aspect of the sales cycle from prospecting and deal management to forecasting and coaching.

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Timestamps:

0:00 — Trailer

1:28 — Welcome & Introduction

2:43 — When It Started to Click as a Leader

4:18 — Accountability With Empathy — The Turning Point

5:48 — How He Actually Implemented Change

7:47 — From Compliance to Commitment

8:31 — Leaning on Mentors Through the Hard Moments

9:09 — The App Dynamics Story — A Baptism of Fire

12:34 — What Made Him Choose App Dynamics Over MongoDB & Medallia

14:52 — Why Dolly Said He Wasn't Ready

16:05 — The Rise to Third Line — Zigs, Zags & Getting Passed Over

18:11 — How to Systematically Build a Team From Scratch

20:21 — The Power of Activity Data & Leading Indicators

22:55 — When Did He Know He Wanted to Be a CRO?

25:08 — Was He Always Chasing the Title?

28:50 — Playbook First, Domain Second

32:18 — How Important Is Founder Support for Your Strategy?

33:39 — The Critical Criteria When Assessing a CRO Opportunity

35:24 — How to Assess a Founder Before You're In

38:03 — What Drew Him to Endor Labs

40:07 — The Four Problems Endor Is Built to Solve

43:49 — How Endor Stands Up Against the Big Players

46:10 — What's Stopping a Foundational Model From Doing This?

48:04 — Where Endor Is on the Journey & What's Next

49:44 — Why Endor Is a Great Place for Sales Leaders Right Now

51:18 — Closing